1,1'-Carbonyldiimidazole → Ethyl 2-(6-bromo-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)acetate

HRID 2172072Notes

Reaction equation

HRID 2172072 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][C:14]1[C:19]([CH2:20][NH:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][C:17]([Br:28])=[CH:16][N:15]=1>O1CCOCC1>[Br:28][C:17]1[CH:16]=[N:15][C:14]2[NH:13][C:6](=[O:7])[N:21]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:20][C:19]=2[CH:18]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59456921Ethyl 2-((2-amino-5-bromopyridin-3-yl)methylamino)acetate

Product 1

HCID 66966289Ethyl 2-(6-bromo-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)acetateYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

CDI (1.8 g, 114 mmol) was added to a solution of ethyl 2-((2-amino-5-bromopyridin-3-yl)methylamino)acetate (1.1 g, 38.17 mmol) in dioxane (36 mL). The reaction mixture was stirred at reflux for 5 hours and then concentrated to dryness. The residue was partitioned between dichloromethane (40 mL) and water (30 mL). The aqueous phase was separated and extracted with dichloromethane (2×30 mL). The combined organic phases were washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The isolated compound was finally precipitated from a mixture dichloromethane/pentane to give the title product as a yellow solid (670 mg, 56%).

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between dichloromethane (40 mL) and water (30 mL)
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane (2×30 mL)
  6. washThe combined organic phases were washed with brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe isolated compound was finally precipitated from a mixture dichloromethane/pentane

Sources & evidence

ORD record
ord-dc9b4c42b4654ee1b8dd75bfa5709af1
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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